Potassium Phosphate, Tribasic → (4-isopropyl-piperazin-1-yl)-(3-methyl-2-o-tolyl-3H-imidazol-4-yl)-methanone

HRID 12449

Reaktionsgleichung

Reaktionsgleichung von HRID 12449
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[C:9]1([CH3:18])[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1B(O)O.Cl[C:20]1[N:24]([CH3:25])[C:23]([C:26]([N:28]2[CH2:33][CH2:32][N:31]([CH:34]([CH3:36])[CH3:35])[CH2:30][CH2:29]2)=[O:27])=[CH:22][N:21]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH:34]([N:31]1[CH2:32][CH2:33][N:28]([C:26]([C:23]2[N:24]([CH3:25])[C:20]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[CH3:18])=[N:21][CH:22]=2)=[O:27])[CH2:29][CH2:30]1)([CH3:36])[CH3:35]

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 27332672-Methylphenyl boronic acidHCID 59338485(2-chloro-3-methyl-3H-imidazol-4-yl)-(4-isopropyl-piperazin-1-yl)-methanone

Produkt 1

HCID 59337779(4-isopropyl-piperazin-1-yl)-(3-methyl-2-o-tolyl-3H-imidazol-4-yl)-methanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A reaction vessel is charged with Pd2(dba)3 (0.0183 g, 0.02 mmol), P(t-Bu)3HBF4 (0.0116 g, 0.04 mmol), K3PO4 (0.127 g, 0.60 mmol), o-tolylboronic acid (0.0408 g, 0.30 mmol) and (2-chloro-3-methyl-3H-imidazol-4-yl)-(4-isopropyl-piperazin-1-yl)-methanone (0.0542 g, 0.20 mmol). Toluene (2.4 mL, anhydrous) is added and the reactor is flushed and sealed under argon. The reaction is stirred at 100° C. for 16 hr; then at rt water (2 mL) and isopropyl acetate (1 mL) are added. The organic layer is removed and the aqueous layer is reextracted with isopropyl acetate. The combined organic extracts are passed through a plug of celite with EtOAc as the eluent. The filtered solution is concentrated to ˜⅓ volume in vacuo and the resulting solution is purified via SCX solid phase extraction. Purification of this crude product via preparative LC-MS gives (4-isopropyl-piperazin-1-yl)-(3-methyl-2-o-tolyl-3H-imidazol-4-yl)-methanone. LC-MS (M+1) 327.3.

Aufarbeitung

  1. customthe reactor is flushed
  2. customsealed under argon
  3. additionthen at rt water (2 mL) and isopropyl acetate (1 mL) are added
  4. customThe organic layer is removed
  5. concentrationThe filtered solution is concentrated
  6. customthe resulting solution is purified via SCX solid phase extraction
  7. customPurification of this crude product via preparative LC-MS

Quellen und Nachweise

ORD-Eintrag
ord-a881f7fabe29446d94622d478d282695
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728009B1

Verknüpfte Notizen

Wird geladen…